Transportation management systems provide support for the logistical issues in managing the transportation of persons, cargo or the like. In some transportation management systems, a driver provides transportation services to a rider to a location selected by the rider; the particular instance of driver transporting a rider is called a trip. In typical systems, when transporting the rider to the selected location, the driver follows her personal preferences in selecting the route to the selected location or follows a route provided by a mapping service. In order to travel a route preferred by the rider, the rider, in such systems, would have to explicitly ask the driver to use the preferred route. This not only requires the rider to be aware of alternative routes and her preferences, but also engage in an undesirable interaction with the driver.